40188-88-3

Upstream product

• 35151-94-1 2-hydroxymethyl-5-n-pentadecylphenol 
• 501-26-8 3-[(Z)-8-pentadecenyl]phenol 
• 50-00-0 formaldehyd 
• 501-24-6 3-n-Pentadecylphenol 
• 67-66-3 chloroform 

Downstream Products

• 35151-94-1 2-hydroxymethyl-5-n-pentadecylphenol 

Relevant academic research and scientific papers

Stimuli responsive hydrogels derived from a renewable resource: synthesis, self-assembly in water and application in drug delivery

We designed and synthesised coumarin-tris derivatives from a renewable resource and well characterized them using different spectral techniques. The self-assembly of coumarin-tris amphiphiles into hydrogels was examined relative to the molecular structure

Morphology transition in helical tubules of a supramolecular gel driven by metal ions

Our aim to access a particular chemical functionality on helical tubules has been achieved by the rational molecular design and synthesis of glucono-appended cardanol derivatives. For the first time, we report a chiral molecular packing with α-helical tub

Structural, photophysical and electrochemical properties of a novel cardanol-based salophen ligand and its Mn(II) complex

A new cardanol-based salophen (hpbp) ligand and its manganese complex [Mn(hpbp)] were obtained by microwave-assisted synthesis method, with yields and reaction times of 65% in 20 min and 85% in 5min, respectively. The structural features of compounds were

Potent nematicidal activity of phthalaldehyde, salicylaldehyde, and cinnamic aldehyde against Meloidogyne incognita

The nematicidal activity of selected aromatic aldehydes was tested against the root knot nematode Meloidogyne incognita. The most active aldehyde was phthalaldehyde (1) with an EC50 value of 11 ± 6 mg/L followed by salicylaldehyde (2) and cinnamic aldehyde (3) with EC50 values of 11 ± 1 and 12 ± 5 mg/L, respectively. On the other hand, structurally related aldehydes such as 2-methoxybenzaldehyde (21), 3,4-dimethoxybenzaldehyde, and vanillin (23) were not active at the concentration of 1000 mg/L. By liquid chromatography-mass spectrometry the reactivity of tested aldehydes against a synthetic peptide resembling the nematode cuticle was characterized. At the test concentration of 1 mM, the main adduct formation was observed for 3,4-dihydroxybenzaldehyde (22), 2-methoxybenzaldehyde (21), and 3,4-dimethoxybenzaldehyde. Considering that 2-methoxybenzaldehyde (21) and 3,4-dimethoxybenzaldehyde were not active against M. incognita in in vitro experiments led us to hypothesize a different mechanism of action rather than an effect on the external cuticle modification of nematodes. When the toxicity of the V-ATPase inhibitor pyocyanin (10) was tested against M. incognita J2 nematodes, an EC50 at 24 h of 72 ± 25 mg/L was found. The redox-active compounds such as phthalaldehyde (1) and salicylaldehyde (2) may share a common mode of action inhibiting nematode V-ATPase enzyme. The results of this investigation reveal that aromatic redox-active aldehydes can be considered as potent nematicides, and further investigation is needed to completely clarify their mode of action.

Phenolic Lipids Derived from Cashew Nut Shell Liquid to Treat Metabolic Diseases

Metabolic diseases are increasing at staggering rates globally. The peroxisome proliferator-activated receptors (PPARα/γ/δ) are fatty acid sensors that help mitigate imbalances between energy uptake and utilization. Herein, we report compounds derived from phenolic lipids present in cashew nut shell liquid (CNSL), an abundant waste byproduct, in an effort to create effective, accessible, and sustainable drugs. Derivatives of anacardic acid and cardanol were tested for PPAR activity in HEK293 cell co-transfection assays, primary hepatocytes, and 3T3-L1 adipocytes. In vivo studies using PPAR-expressing zebrafish embryos identified CNSL derivatives with varying tissue-specific activities. LDT409 (23) is an analogue of cardanol with partial agonist activity for PPARα and PPARγ. Pharmacokinetic profiling showed that 23 is orally bioavailable with a half-life of 4 h in mice. CNSL derivatives represent a sustainable source of selective PPAR modulators with balanced intermediate affinities (EC50 ～100 nM to 10 μM) that provide distinct and favorable gene activation profiles for the treatment of diabetes and obesity.

COMPOUNDS HAVING EXCITED STATE INTRAMOLECULAR PROTON TRANSFER (ESIPT) CHARACTER FOR USE IN TREATING AND/OR PREVENTING SUNBURN AND/OR PREVENTING U.V. DAMAGE

This disclosure relates to use of cashew nut shell liquid (CNSL) phenolics in the manufacture of molecules having ESIPT character, wherein said molecules are UVA and/or UVB absorbers, and further wherein said molecules are formulated as protectants against UVA and/or UVB radiation. The disclosure extends to use of CNSL in the manufacture of compositions including molecules having ESIPT character for treating and/or preventing sunburn and/or preventing U.V. damage.

Cardanol Schiff base antioxidant as well as preparation method and application thereof

The invention discloses a cardanol Schiff base antioxidant, which comprises a compound having a structure represented by the formula shown in the specification, wherein R is selected from any one of the structures shown in the specification, R1 is independently selected from H or the structure represented by the structure shown in the specification. The invention also discloses a method for preparing the cardanol Schiff base antioxidant. The cardanol Schiff base antioxidant disclosed by the invention has excellent thermal stability and good oxidation resistance and corrosion resistance, the preparation process is simple and feasible, the reaction conditions are mild and rapid, and the aftertreatment is simple and convenient. The cardanol Schiff base antioxidant disclosed by the invention is suitable for being widely applied to the fields of lubricating oil, lubricating grease and the like.

Valorisation of Cashew Nut Shell Liquid Phenolics in the Synthesis of UV Absorbers

With current concerns over the use of fossil resources for chemical synthesis of functional molecules and the effect of current UV absorbers in sunscreens have on the ecosystem, we describe a xylochemical synthesis of different classes of aromatic UV absorbers utilizing cashew nut shell liquid as a non-edible bio-renewable carbon source. Hydroxybenzophenones, xanthones, triazines, and flavones were synthesized starting from cardanol or anacardic acid. Several compounds exhibited favorable UVA and UVB absorption characteristics.

Strongly fluorescent organogels and self-assembled nanostructures from pyrene coupled coumarin derivatives: Application in cell imaging

Three different coumarin coupled pyrene derivatives with varying hydrophobic units (alkyl chains) have been synthesised and well characterized using NMR and mass spectral analysis. The gelation behaviour and self-aggregation properties of these compounds were studied relative to the molecular structure and solvent affinity. Among these derivatives, the one which is not having any hydrophobic tail displays efficient gelation in higher alcohols such as decanol and dodecanol. However the other derivatives having saturated and unsaturated hydrophobic tails form weak gel in different solvents. The morphology of gel was investigated by optical microscopy and high resolution transmission electron microscopy (HRTEM). The investigation of absorption and emission spectra of these compounds revealed that the photo-physical properties were significantly influenced by the self-assembly process in different solvents. The concentration dependent emission and 1H NMR studies clearly suggest that the π-π stacking interaction and hydrogen bonding between carbonyl groups of coumarin coupled pyrene with the -OH group of solvent were the driving forces for the process of gelation and self-aggregation. Rheological investigation clearly demonstrates the flow behaviour and reversible nature of organogel under temperature and strain ramp up and ramp down experimental conditions. By getting clue from the self-assembly mechanism in different solvents, we derived nano-flakes from coumarin coupled pyrene derivatives and further explored their potential applications in the field of cell imaging. The size of the self-aggregated particles in the DMSO-water mixture has been identified using HRTEM and a zetasizer. The nanomaterials obtained via the self-assembly process were used for fibroblast and PC3 prostate cancer cell imaging applications. Further investigation reveals that these compounds suppress the proliferation of PC3 cells.

The synthesis of 2-hydroxymethyl derivatives of phenols

2-Hydroxymethylphenols have been prepared in good yield by reduction with sodium borohydride of the precursor aldehydes, obtained regiospecifically from reaction of phenols with paraformaldehyde in toluene containing stannic chloride and tri-n-butylamine. By contrast, reaction of phenols with either paraformaldehyde under anhydrous conditions or with aqueous formaldehyde results in formation of both the hydroxymethyl and the bishydroxymethyl derivatives. Cyclic acetals of the precursor aldehydes are readily accessible.